[ CAS No. 351-30-4 ] {[proInfo.proName]}

Name: 351-30-4|N-(4-Bromo-3-fluorophenyl)acetamide|95%
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Quality Control of [ 351-30-4 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 351-30-4 ]

CAS No. :	351-30-4	MDL No. :	MFCD00672937
Formula :	C₈H₇BrFNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GAQUWJRFYLETKX-UHFFFAOYSA-N
M.W :	232.05	Pubchem ID :	2773316
Synonyms :

Safety of [ 351-30-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340-P405-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 351-30-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 351-30-4 ]
Downstream synthetic route of [ 351-30-4 ]

[ 351-30-4 ] Synthesis Path-Upstream 1~4

1
[ 351-30-4 ]
[ 656-65-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride; water In ethanol at 80℃; for 4 h;	To a stirred solution of N-(4-bromo-3-fluorophenyl)acetamide (12.9 g, 12.9 mmol) dissolved in ethanol (30 mL), conc. HCI (15 mL) was added and refluxed at 80 °C for4 h. The reaction mixture diluted ice water and extracted with ethyl acetate, the combined organic layer was washed with water and brine solution. The solvent was removed under vacuo to yield the title compound (2.45 g, 100.0percent) as an off white solid.

Reference： [1] Patent: WO2014/202580, 2014, A1, . Location in patent: Page/Page column 97; 98
[2] Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 204, p. 43 - 64
[3] Journal of the Chemical Society, 1958, p. 2815,2818

2
[ 351-30-4 ]
[ 136434-77-0 ]

Reference： [1] Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 204, p. 43 - 64

3
[ 351-30-4 ]
[ 153505-36-3 ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: at 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 120℃; for 0.333333 h; Microwave irradiation Stage #3: With sodium hydrogencarbonate In tetrahydrofuran; water	INTERMEDIATE 16; 4-Bromo-5-fluoro-2-nitrophenylaminePotassium nitrate (914 mg, 9.05 mmol) was added to a stirred solution of 4-bromo- 3-fluoroacetanilide (2 g, 8.6 mmol) in sulfuric acid (10 mL) at r.t. After 1.5 h the mixture was poured onto ice (approximately 100 g) and extracted with EtOAc (100 mL). The organic phase was dried (MgSO₄) and the solvent removed in vacuo to give a brown solid (2.48 g). 1.9 g of this material was dissolved/suspended in THF (10 mL). Hydrochloric acid (2M, 10 mL) was added, and the mixture heated in a microwave for 20 minutes at 12O⁰C. The mixture was partitioned between EtOAc and sodium hydrogencarbonate solution (100 mL each) and the aqueous phase extracted with EtOAc (50 mL). The combined organic phases were dried (MgSO₄) and the solvent removed in vacuo. The residue was purified by column chromatography (SiO₂, 10 to 100percent EtOAc in heptane) to give an orange-brown solid (1.5 g) which was washed with 9:1 heptane:diethyl ether to give, after air-drying, the title compound (900 mg, 45percent) as an orange-yellow solid. 6_H (CDCl₃) 8.39 (d, IH), 6.59 (d, IH), 6.21 (br, 2H).

Reference： [1] Patent: WO2010/52448, 2010, A2, . Location in patent: Page/Page column 40-41

4
[ 351-30-4 ]
[ 1219741-79-3 ]

Reference： [1] Patent: WO2014/202580, 2014, A1,

[ 351-30-4 ] Synthesis Path-Downstream 1~24

1
[ 351-28-0 ]
[ 351-30-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With N-Bromosuccinimide In dichloromethane a) reflux, 5 h, b) room temp., 16 h;
97%	With Eosin Y; Selectfluor In acetonitrile at 25℃; for 2h; regioselective reaction;
78%	With bis-[(trifluoroacetoxy)iodo]benzene; sodium bromide In ethanol at 25℃; for 1h; Green chemistry; regioselective reaction;

37.73%	With N-Bromosuccinimide In dichloromethane at 60℃; for 24h;	Intermediate 30b: N-(4-Bromo-3-fluorophenyl)acetamide To stirred solution of N-(3-fluorophenyl)acetamide (7.0 g, 45.7 mmol) in DCM (50mL), NBS (8.13 g, 1.0 eq) was added and heated at 60 °C for 24 h. The reactionmixture was diluted with water DCM and was washed with water and brine solution. The solvent was removed under vacuo. The product was purified by column chromatography to yield the title compound (4.0 g, 37.73%) as an off white solid. 1H NMR: (DMSO-d6, 300MHz) 6 10.28(s, 1H), 7.73-7.78 (dd, 1H), 7.57-7.63 (t, 1H),7.24-7.28 (dd, 1 H), 2.07 (5, 3H).
	With N-Bromosuccinimide

Reference： [1]Gray, G. W.; Hird, M.; Toyne, K. J. [Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 204, p. 43 - 64]
[2]Huang, Binbin; Zhao, Yating; Yang, Chao; Gao, Yuan; Xia, Wujiong [Organic Letters, 2017, vol. 19, # 14, p. 3799 - 3802]
[3]Tian, Chao; Yao, Xu; Ji, Weizhe; Wang, Qian; An, Guanghui; Li, Guangming [European Journal of Organic Chemistry, 2018, vol. 2018, # 43, p. 5972 - 5979]
[4]Current Patent Assignee: CONNEXIOS LIFE SCIENCES PVT - WO2014/202580, 2014, A1 Location in patent: Page/Page column 97
[5]Buu-Hoi et al. [Journal of the Chemical Society, 1958, p. 2815,2818]

2
[ 351-30-4 ]
[ 656-65-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride; water In ethanol at 80℃; for 4h;	Intermediate 30c: 4-Bromo-3-fluoroaniline To a stirred solution of N-(4-bromo-3-fluorophenyl)acetamide (12.9 g, 12.9 mmol) dissolved in ethanol (30 mL), conc. HCI (15 mL) was added and refluxed at 80 °C for4 h. The reaction mixture diluted ice water and extracted with ethyl acetate, the combined organic layer was washed with water and brine solution. The solvent was removed under vacuo to yield the title compound (2.45 g, 100.0%) as an off white solid.
99%	With hydrogenchloride In ethanol for 2h; Heating;

Reference： [1]Current Patent Assignee: CONNEXIOS LIFE SCIENCES PVT - WO2014/202580, 2014, A1 Location in patent: Page/Page column 97; 98
[2]Gray, G. W.; Hird, M.; Toyne, K. J. [Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 204, p. 43 - 64]
[3]Buu-Hoi et al. [Journal of the Chemical Society, 1958, p. 2815,2818]

3
[ 372-19-0 ]
[ 351-30-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 70 percent / acetic acid / 0.33 h / Heating 2: 100 percent / NBS / CH₂Cl₂ / a) reflux, 5 h, b) room temp., 16 h
	Multi-step reaction with 2 steps 1: acetic acid / 3 h / 105 °C 2: N-Bromosuccinimide / dichloromethane / 24 h / 60 °C
	Multi-step reaction with 2 steps 1: triethylamine / ethyl acetate / 0 - 25 °C 2: Eosin Y; Selectfluor / acetonitrile / 2 h / 25 °C

Reference： [1]Gray, G. W.; Hird, M.; Toyne, K. J. [Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 204, p. 43 - 64]
[2]Current Patent Assignee: CONNEXIOS LIFE SCIENCES PVT - WO2014/202580, 2014, A1
[3]Huang, Binbin; Zhao, Yating; Yang, Chao; Gao, Yuan; Xia, Wujiong [Organic Letters, 2017, vol. 19, # 14, p. 3799 - 3802]

4
[ 351-30-4 ]
[ 136434-77-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 99 percent / 36percent HCl / ethanol / 2 h / Heating 2: 1) 36percent HCl, NaNO₂, 2) KI / 1) H₂O, 0 deg C, 20 min, 2) H₂O, cyclohexane, room temp., 16 h

Reference： [1]Gray, G. W.; Hird, M.; Toyne, K. J. [Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 204, p. 43 - 64]

5
[ 351-30-4 ]
[ 136434-78-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 99 percent / 36percent HCl / ethanol / 2 h / Heating 2: 1) 36percent HCl, NaNO₂, 2) KI / 1) H₂O, 0 deg C, 20 min, 2) H₂O, cyclohexane, room temp., 16 h

Reference： [1]Gray, G. W.; Hird, M.; Toyne, K. J. [Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 204, p. 43 - 64]

6
[ 351-30-4 ]
[ 136434-79-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 99 percent / 36percent HCl / ethanol / 2 h / Heating 2: 1) 36percent HCl, NaNO₂, 2) KI / 1) H₂O, 0 deg C, 20 min, 2) H₂O, cyclohexane, room temp., 16 h 4: 96 percent / H₂ / PtO₂ / ethanol / 2 h / 760 Torr / Ambient temperature

Reference： [1]Gray, G. W.; Hird, M.; Toyne, K. J. [Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 204, p. 43 - 64]

7
[ 351-30-4 ]
[ 3851-45-4 ]

Reference： [1]Buu-Hoi et al. [Journal of the Chemical Society, 1958, p. 2815,2818]

8
[ 128-08-5 ]
[ 351-30-4 ]

Yield	Reaction Conditions	Operation in experiment
20.40 g (100%)	In dichloromethane	1 Step 1.2 4-Bromo-3-fluoroacetanilide Step 1.2 4-Bromo-3-fluoroacetanilide N-Bromosuccinimide (15.73 g, 0.088 mol) is added all at once to a stirred solution of compound 1.1 (13.50 g, 0.088 mol) in dry dichloromethane at room temperature. The stirred mixture is heated under reflux for 5 hours (glc analysis showing a complete reaction and the presence of only one product peak) cooled and washed with lots of water. The aqueous extract is washed with dichloromethane and the combined organic extracts are washed with water and dried (MgSO4). The solvent is removed in vacuo to give a pale orange solid, and a further sample can then recrystallized from hexane/dimethoxyethane (99:1) to yield colourless crystals, giving a yield of 20.40 g (100%).

Reference： [1]Current Patent Assignee: INNOLUX CORP. - US5888421, 1999, A

9
[ 351-30-4 ]
[ 153505-36-3 ]

Yield	Reaction Conditions	Operation in experiment
45%		INTERMEDIATE 16; 4-Bromo-5-fluoro-2-nitrophenylaminePotassium nitrate (914 mg, 9.05 mmol) was added to a stirred solution of 4-bromo- 3-fluoroacetanilide (2 g, 8.6 mmol) in sulfuric acid (10 mL) at r.t. After 1.5 h the mixture was poured onto ice (approximately 100 g) and extracted with EtOAc (100 mL). The organic phase was dried (MgSO4) and the solvent removed in vacuo to give a brown solid (2.48 g). 1.9 g of this material was dissolved/suspended in THF (10 mL). Hydrochloric acid (2M, 10 mL) was added, and the mixture heated in a microwave for 20 minutes at 12O0C. The mixture was partitioned between EtOAc and sodium hydrogencarbonate solution (100 mL each) and the aqueous phase extracted with EtOAc (50 mL). The combined organic phases were dried (MgSO4) and the solvent removed in vacuo. The residue was purified by column chromatography (SiO2, 10 to 100% EtOAc in heptane) to give an orange-brown solid (1.5 g) which was washed with 9:1 heptane:diethyl ether to give, after air-drying, the title compound (900 mg, 45%) as an orange-yellow solid. 6H (CDCl3) 8.39 (d, IH), 6.59 (d, IH), 6.21 (br, 2H).

Reference： [1]Patent: WO2010/52448,2010,A2 .Location in patent: Page/Page column 40-41

10
[ 351-30-4 ]
[ 33513-42-7 ]
[ 1309365-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate at 75℃; for 48.5h; Inert atmosphere; Sealed tube; Cooling with ice;	VII.1 Step 1; DMF (54 ml, 701 mmol, 2.5 eq.) was added dropwise (via a syringe pump) to phosphoryl trichloride (179 ml, 1962 mmol, 7.0 eq.) in a 350 mL sealed tube in an ice bath under nitrogen. After the addition, the water bath was removed and N-(3-fluoro-4- bromophenyl)acetamide (65 g, 280 mmol) was added in one portion and stirred until a homogenous solution was observed (approx. 30 min.). The reaction vessel was sealed and heated at 75 °C for 48 h. The reaction was allowed to cool and slowly poured onto ice(final volume of 2 L) and stirred for 25 min. The solid was filtered and washed with water until the filtrate was no longer acidic (~3 L) and the product was dried in an oven vacuum overnight at 50 °C to afford a light tan/gold colored solid, 6-bromo-2-chloro-7- fluoroquinoline-3-carbaldehyde.

Reference： [1]Current Patent Assignee: AMGEN INC - WO2011/63233, 2011, A1 Location in patent: Page/Page column 46

11
[ 351-30-4 ]
[ 1309365-71-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 48.5 h / 75 °C / Inert atmosphere; Sealed tube; Cooling with ice 2: ethanol / 2.5 h / 125 °C / Sealed tube